First total synthesis of (+)-vedelianin, a potent antiproliferative agent

Joseph J. Topczewski; David F. Wiemer

doi:10.1016/j.tetlet.2011.01.137

First total synthesis of (+)-vedelianin, a potent antiproliferative agent

Joseph J. Topczewski
, David F. Wiemer

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

22 Scopus citations

Abstract

The total synthesis of (+)-vedelianin has been accomplished in 18 steps from vanillin. Preparation of a key intermediate in nonracemic form through a Shi epoxidation has allowed determination of the absolute stereochemistry of the natural product as the (2S,3R,4aR,9aR)-isomer.

Original language	English (US)
Pages (from-to)	1628-1630
Number of pages	3
Journal	Tetrahedron Letters
Volume	52
Issue number	14
DOIs	https://doi.org/10.1016/j.tetlet.2011.01.137
State	Published - Apr 6 2011

Bibliographical note

Funding Information:
We thank Dr. John A. Beutler (NCI–Frederick), Dr. Odile Thoisson, and Dr. Françoise Gueritte (ISCN CNRS, Gif-sur-Yvette, France) for sharing data on the activity of (+)-vedelianin in the NCI 60 cell line screen, Dr. John G. Kodet for providing the initial vanillin derivative, and Dr. Nolan R. Mente for providing phosphonate 18 . Financial support in the form of an ACS Division of Medicinal Chemistry predoctoral fellowship (to J.J.T.), a Shriner Fellowship from the University of Iowa (to J.J.T.), from the Roy J. Carver Charitable Trust, and the NIH (R41CA126020 via Terpenoid Therapeutics, Inc.) is gratefully acknowledged.

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title = "First total synthesis of (+)-vedelianin, a potent antiproliferative agent",

abstract = "The total synthesis of (+)-vedelianin has been accomplished in 18 steps from vanillin. Preparation of a key intermediate in nonracemic form through a Shi epoxidation has allowed determination of the absolute stereochemistry of the natural product as the (2S,3R,4aR,9aR)-isomer.",

author = "Topczewski, \{Joseph J.\} and Wiemer, \{David F.\}",

note = "Funding Information: We thank Dr. John A. Beutler (NCI–Frederick), Dr. Odile Thoisson, and Dr. Fran{\c c}oise Gueritte (ISCN CNRS, Gif-sur-Yvette, France) for sharing data on the activity of (+)-vedelianin in the NCI 60 cell line screen, Dr. John G. Kodet for providing the initial vanillin derivative, and Dr. Nolan R. Mente for providing phosphonate 18 . Financial support in the form of an ACS Division of Medicinal Chemistry predoctoral fellowship (to J.J.T.), a Shriner Fellowship from the University of Iowa (to J.J.T.), from the Roy J. Carver Charitable Trust, and the NIH (R41CA126020 via Terpenoid Therapeutics, Inc.) is gratefully acknowledged. ",

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doi = "10.1016/j.tetlet.2011.01.137",

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AU - Wiemer, David F.

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N2 - The total synthesis of (+)-vedelianin has been accomplished in 18 steps from vanillin. Preparation of a key intermediate in nonracemic form through a Shi epoxidation has allowed determination of the absolute stereochemistry of the natural product as the (2S,3R,4aR,9aR)-isomer.

AB - The total synthesis of (+)-vedelianin has been accomplished in 18 steps from vanillin. Preparation of a key intermediate in nonracemic form through a Shi epoxidation has allowed determination of the absolute stereochemistry of the natural product as the (2S,3R,4aR,9aR)-isomer.

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First total synthesis of (+)-vedelianin, a potent antiproliferative agent

Abstract

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